Hydrochloric Acid → HCID 44547911, compound

HRID 1512887Notes

Reaction equation

HRID 1512887 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:27]=3[N:26]([CH:28]([CH3:30])[CH3:29])[CH:25]=[C:24]4[CH2:31][CH2:32][C:33]([O:35]C(C)C)=[O:34])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].Cl>C1COCC1.C(O)(C)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:27]=3[N:26]([CH:28]([CH3:29])[CH3:30])[CH:25]=[C:24]4[CH2:31][CH2:32][C:33]([OH:35])=[O:34])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59146058HCID 59146058, compound

Product 1

HCID 44547911HCID 44547911, compoundYield 50.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (93 mg) was added to a solution of 1-methylethyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-(1-methylethyl)-1H-indol-3-yl]propanoate (D122) (60 mg) in THF (5 mL), isopropanol (4 mL) and water (2 mL). The reaction mixture was stirred at room temperature for 2 days. The mixture was neutralized with 2 M HCl till pH ˜6.0. The solvent was concentrated, and the residue was dissolved in water. The precipitated solid was purified by Mass Directed Auto Prep to afford 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-(1-methylethyl)-1H-indol-3-yl]propanoic acid (E28) (28 mg). δH (DMSO-d6, 400 MHz): 1.30 (6H, d), 1.37 (6H, d), 2.64 (2H, t), 3.00 (2H, t), 4.56 (1H, m), 4.89 (1H, m), 7.16 (1H, t), 7.37 (1H, dd), 7.46 (2H, m), 7.79 (1H, dd), 8.12 (1H, dd), 8.18 (1H, d), 12.07 (1H, br s); MS (ES): C26H26ClN3O4 requires 467; found 468.2 (M+H+).

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in water
  3. customThe precipitated solid was purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-d8d94b548ac44859b9e4ea4e200c5dc2
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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